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F. Scott Fitzgerald’s magical short story “The Curious Case of Benjamin Button” was a hard sell during the early days of the Roaring ‘20s, when magazines were hungering for one of the author’s more down-to-earth flapper stories.

“Benjamin Button” was a rare foray for Fitzgerald into the fantasy genre -- a quixotic tale of a man who was born with the body of an old man and grew younger as the years passed. “Button” finally found a home at Collier’s, which published it on May 27, 1922.

According to Fitzgerald scholar Matthew J. Bruccoli, Fitzgerald was “probably attracted to this form by its tension between romanticism and realism, for the challenge of fantasy is to make events convincing.”

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Now this most unusual tale from the iconic author of “The Great Gatsby,” “Tender Is the Night” and “The Last Tycoon” may finally accomplish something that no other adaptation of a Fitzgerald story or novel has done: become a serious Oscar contender.

Though the lavish, special-effects-driven film adaptation directed by David Fincher and starring Brad Pitt as Button opened to mixed reviews, the fable has already scored nominations for the Golden Globes, Screen Actors Guild Awards and the Broadcast Film Critics Assn. Critics’ Choice Awards.

Hollywood set its sights on Fitzgerald as early as 1920. In the last 88 years, there have been myriad film and TV adaptations of his short stories and novels. Some worked, but many others strayed badly off the mark, perhaps because the novelist’s poetic language and singular sensibility are difficult to duplicate on screen.

Fitzgerald became a member of the “lost generation” of novelists and playwrights who came to Hollywood in the 1930s to try their luck -- and help their dwindling coffers -- at screenwriting. But Fitzgerald’s stint at MGM was short-lived and disappointing. His only screen credit was for co-writing the post-World War I love story “Three Comrades.”

When Fitzgerald collected “Button” in his classic 1922 “Tales of the Jazz Age” anthology, he noted that “the story was inspired by a remark of Mark Twain’s to the effect that it was pity that the best part of life came at the beginning and the worst part at the end. By trying the experiment upon only one man in a perfectly normal world I have scarcely given his idea a fair trial.”

Fitzgerald, who long battled alcoholism, died on Dec. 21, 1940, at the age of 44 at the Hollywood apartment of his lover, Sheilah Graham. Just as Twain had said, the worst part of his life came at the end.

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Here’s a look at few of the adaptations of Fitzgerald’s work in film and on TV.

‘The Great Gatsby’

Fitzgerald’s most famous work, this 1925 love story tells the tale of mysterious, wealthy bootlegger Jay Gatsby, who becomes entwined in the tangled life of his ex-lover, Daisy Buchanan.

A year after its publication, Herbert Brenon directed the first feature film version with Warner Baxter as Gatsby and Lois Wilson as Daisy. Unfortunately, the film has not survived the ravages of time -- only a trailer exists of the silent.

What many feel was the best version was produced by Paramount in 1949 with Alan Ladd receiving some of the strongest reviews of his career as Gatsby. Directed by Elliott Nugent, the film also starred Betty Field as Daisy, as well as Macdonald Carey, Ruth Hussey, Shelley Winters and Barry Sullivan. Unfortunately, before the release of Paramount’s 1974 version, the studio took all the prints of this one out of circulation and banned it from being shown on TV. It has yet to emerge on DVD.

That’s particularly unfortunate since the much-hyped 1974 adaptation starring Robert Redford was mediocre at best. Despite a stellar cast that included Redford as Gatsby and Mia Farrow as Daisy, a script by Francis Ford Coppola and direction from noted British filmmaker Jack Clayton, this lush romance laid an egg with critics and audiences.

Then in 2001, A&E; aired a ho-hum British adaptation with Toby Stephens as Gatsby and Mira Sorvino as Daisy. But there’s still hope for “Gatsby” lovers; Baz Luhrmann has supposedly signed up to direct a new screen version. Let’s hope it’s more like his “Romeo + Juliet” and less like “Australia.”

‘The Last Time I Saw Paris’

Richard Brooks directed this satisfying 1954 version of Fitzgerald’s 1931 short story “Babylon Revisited,” considered by Bruccoli to be one of the writer’s “half-dozen greatest stories. Like all of his best fiction it was intensely personal, expressing his feelings about his alcoholism, his wife’s mental collapse and his responsibility to his daughter.”

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Though the short story is set during the 1920s, Brooks’ beautifully acted adaptation begins in post-World War II when Charles (Van Johnson), a GI with writing ambitions, goes to Paris to pen a novel and falls in love and marries the beautiful Helen (Elizabeth Taylor). They soon have a child, but their happiness is short-lived when Charles begins to hit the bottle when he can’t sell his stories.

Taylor later told an interviewer that the film “first convinced me I wanted to be an actress, instead of yawning my way through parts.”

‘Tender Is the Night’

“Tender Is the Night” is also considered one of Fitzgerald’s masterpieces. It was Fitzgerald’s first novel in nine years and the last he completed. He began working on the novel in 1932 when his wife, Zelda, was hospitalized for schizophrenia in Baltimore.

The lengthy, bleak novel revolves around the rise and fall of a young psychologist named Dick Diver and his wife, Nicole, who was one of his patients. In 1962, Henry King directed the exquisitely shot but overly sentimental version with Jennifer Jones as Nicole and Jason Robards as Dick. The title song by Sammy Fain and Paul Francis Webster earned an Oscar nomination.

Far superior was a 1985 British miniseries adapted by Dennis Potter (“The Singing Detective”) that was telecast on Showtime. Mary Steenburgen and Peter Strauss were lauded for their performances as Nicole and Dick. The miniseries was repeated only once, on Bravo, and has never been released on DVD.

‘The Last Tycoon’

Fitzgerald died while he as working on this novel about Monroe Stahr -- loosely based on MGM’s Irving Thalberg -- a powerful young film executive working in Hollywood in the 1930s.

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Fitzgerald’s friend, literary critic Edmund Wilson, collected and edited Fitzgerald’s notes, and the book was published in 1941. In 1957, John Frankenheimer directed a vivid “Playhouse 90” live version of “Tycoon” with Jack Palance as Stahr.

In 1976, Elia Kazan (“On the Waterfront”) directed the uneven feature version penned by Harold Pinter and starring Robert De Niro as Stahr. “Tycoon” became the last film directed by the Oscar-winning Kazan.

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susan.king@latimes.com

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